Author: Kunu

Anandamide

N-arachidonoylethanolamine

The Molecule
Of
Extreme Delight

Sujit Kumar Kar
S.K. Foundation, Orissa, India

Anandamide... Let’s think of nomenclature

In the Sanskrit language, Ananda means extreme delight. Anandamide also is important in the regulation of feeding behavior, and the neural generation of motivation and pleasure and thus we find the word Ananda in its common name. According to the nomenclature done by International Union Of Pure And Applied Chemistry, Anandamide has been named as (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide. It is also known as N-arachidonoylethanolamine or AEA. It is also known as “marijuana munchies “ as it enhances food intake in humans and animals.

Structure– Let’s throw Light

From the attached Space fill diagram alongside, we can view that the grayish structures are Carbon atoms. The transparent bubbles denote hydrogen atoms. Blue bubble represents nitrogen atom. The two distinctive red bubbles represent the oxygen atom. From the molecular structure, we can observe that an Oxygen atom is bonded with carbon by means of a double covalent bond.

Space Fill Model Of Anandamide

Molecular Structure Of
Anandamide

Occurrence of Anandamide

Chocolate

Cacao Pods

Anandamide occurs in minute quantities in sea urchin roe. Anandamide was reported to be present in chocolate in small quantities that were assumed not to have pharmacological or psychoactive effects. The human body synthesis Anandamide from N– arachidonoyl phosphatidylethanolamine. In pigs, it is present in endocannabinoids in the brain. In mice, it is present in liver.

Anandamide - As an inhibitor

It inhibits human breast cancer cell proliferation.
It inhibits cholangiocarcinoma (Cancer of bile ducts) via activation of the noncanonical Wnt signaling pathway (a complex of network proteins well known for their roles in cancer).
Its analog Met-F-AEA controls human breast cancer cell migration via the RHOA/RHO kinase signaling pathway.
It blocks the growth of sheep preimplantation embryos by inducing apoptosis and reversible arrest of cell proliferation.
It inhibits fatty acid amide hydrolase.

Anandamide - Aiding life processes

It induces Apoptosis (programmed cell death in multicellular organisms through phagocytosis or shedding and the disintegration of those cells into membrane bound proteins) in human cells via vanilloid receptors.
It induces cell death in colorectal (relating to both colon and rectum) carcinoma cells (malignant cells in epithelial tissue) and plays a possible role for cyclooxygenase 2(the enzyme that helps mediate inflammation and helps brain feel pain and regulate fever).

So….. they did it

It was isolated and its structure was first described by Czech Analytical chemist Lumír Ondřej Hanuš and American molecular pharmacologist William Anthony Devane in the laboratory of Raphael Mechoulam at the Hebrew University of Jerusalem, Israel in 1992.

Lumír Ondřej Hanuš

Hebrew University of Jerusalem, Israel

Synthesis of Anandamide

Anandamide is synthesized upon demand from phospholipid precursors in cell membranes in response to rise in intracellular calcium levels. It seems that only 1-O-acyl groups of phospholipids such as phosphatidylcholine can serve as acyl donors and that much of the acyl transfer is intramolecular, with production of a hypothetical intermediate, 2-O-acyl-sn-glycero-3-phospho-(N-acyl)- ethanolamine (or N-acyl lysoPE). The free sn-1 hydroxy group is then subjected to reacylation, presumably by the same transacylase system. A second mechanism involves this transacylase catalyzing direct transfer of fatty acids of position 1 of phosphatidylcholine to N-acylate phosphatidylethanolamine. The second stage in the biosynthesis of Anandamide is the hydrolysis of N-acyl phosphatidylethanolamine by a phosphodiesterase that is specific for this lipid. Along with Anandamide, Phosphatidic acid is formed and it also acts as a neurotransmitter.

Synthesis of N-acyl Phophotidylethanolamine

Synthesis of Phosphatidic Acid and Anandamide

Technical Data - Have a glance

Property	Details
Gram Molecular Weight	347.54 grams
Formula	C22H37NO2
Storage	Dessicate at -200C
CAS Number	[94421-68-8]
LD50 Oral Rate	11 milligrams/kg
Physical Appearance	Pale Yellow Oily
Toxicity	Potentially toxic
Stability	Stable at NTP

Let’s peep into Anandamide facts

Anandamide is the Tetrahydrocannabinol like molecule which acts as a neurotransmitter. It is a long chain N-acylethanolamide. Metabotropically, it is a Cannabinoid receptor. It is synthesized enzymatically in the areas of the brain that are important in memory, thought processes and control of movement. So, it can be concluded that the organs of action for Anandamide are cerebrum and cerebellum. Outside the brain, it acts as a chemical messenger between the embryo and uterus during implantation of the embryo in the uterine wall. The highest concentration of it is in the uterus which is found extensively before embryo implantation.

Bibliography

Anandamide— Wikipedia, The Free Encyclopedia
Anandamide- Google Search Results
PNAS— Anandamide
General Chemistry Online—The Bliss Molecule
Biocarta– Anandamide Metabolism

Home

Home

Home

Home